1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18373575, compound

Participants

Reaction Steps

To a solution of 10.0 g (49.7 mmol) of 4-bromo-a-methylbenzyl alcohol and 16.4 g (59.6 mmol) of diphenylphosphoryl azide in 70 mL of toluene was added 9.1 g of 1,8-diazabicyclo[5.4.0]undec-7-ene and the mixture was stirred at room temperature for 16 hours. The reaction mixture was washed once with 30 mL of 10% aqueous sodium bisulfate. The organic layer was separated and the aqueous layer was extracted three times with 10 mL each of ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated in vacuo to afford 11.2 g (100%) of the title compound.

Provenance & Evidence